3483-15-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(o-Methoxyphenyl)sydnone is used as a precursor for the synthesis of various pharmaceuticals due to its ability to form derivatives with potential biological and pharmacological activities. Its unique structure allows for the development of new drugs with improved therapeutic properties.
Used in Dye Industry:
3-(o-Methoxyphenyl)sydnone is used as a precursor for the synthesis of dyes, taking advantage of its chemical properties to create a wide range of colorants for various applications.
Used in Cancer Research:
3-(o-Methoxyphenyl)sydnone is being studied for its potential application in the treatment of cancer. Its unique structure and properties make it a promising candidate for the development of new anticancer drugs.
Used in Antimicrobial Applications:
3-(o-Methoxyphenyl)sydnone has demonstrated antimicrobial properties, making it a compound of interest for further research and development in the field of antimicrobial agents. Its potential use in combating microbial infections could lead to the development of new treatments and preventive measures.
Used in Antioxidant Applications:
3-(o-Methoxyphenyl)sydnone has shown antioxidant properties, which makes it a valuable compound for further research and development in the field of antioxidants. Its potential use in preventing oxidative damage and related diseases could contribute to the development of new health-promoting products and therapies.

Upstream product

• 121163-59-5 N-(2-methoxy-phenyl)-N-nitroso-glycine 
• 108-24-7 acetic anhydride 
• 578-57-4 2-bromoanisole 
• 69825-50-9 ethyl 2-((2-methoxyphenyl)amino)acetate 
• 90-04-0 2-methoxy-phenylamine 
• 94800-23-4 (2-methoxyphenyl)glycine 

Downstream Products

• 269392-84-9 3-(2-methoxy-phenyl)-5-methyl-3H-[1,3,4]oxadiazol-2-one 
• 156333-02-7 C₁₁H₁₀N₂O₄ 
• 60642-51-5 3,3'-bis-(2-methoxy-phenyl)-4,4'-sulfanediyl-bis-sydnone 
• 14606-02-1 4-bromo-3-(2-methoxy-phenyl)-sydnone 

Relevant academic research and scientific papers

Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ

Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.

One-pot conversion of N-arylglycines to sydnones efficiently promoted by bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex Cl2-dabco in the presence of NaNO2/Ac2O under neutral condition

Bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex, (Cl2-DABCO), has been found as an active chlorine complex for effective one-pot conversion of various N-arylglycines to sydnones in high yields (85-95%) under mild and neutral condition.

Synthesis and evaluation of phenyl substituted sydnones as potential DPPH-radical scavengers

A series of phenyl substituted sydnones has been synthesized and their radical-scavenging activity has been studied on DPPH free radical. Out of eighteen compounds screened, nine compounds show interesting activity. A mechanism is presented whereby sydnones scavenge DPPH radical through donating H-atom at 4th-position. Its strong radical-scavenging activity mainly arises from 1, 2, 3-oxadiazolium-5-olate ring. Different substituents and their positions on the phenyl ring differently influence DPPH scavenging activity and therefore, may provide clues to design and develop better free-radical scavenging sydnones with multiple activities.

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS) as an efficient promoter for one-pot conversion of N-arylglycines to sydnones in the presence of NaNO2/Ac2O under neutral conditions

N,N,N′,N′-Tetrabromobenzene-1,3-disolfonamide (TBBDS)-promoted one-pot conversion of various N-arylglycines to sydnones using a combination of NaNO2 and Ac2O has been achieved efficiently through N-nitrosation followed by cyclization

Catalytic activity of 1,3-dibromo-5,5-dimethylhydantoin (DBH) in the one-pot transformation of N-arylglycines to N-arylsydnones in the presence of NaNO2/Ac2O under neutral conditions: Subsequent bromination of these sydnones to their

1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO2 and Ac 2O in high yields (80-

Microwave-assisted synthesis of N-arylglycines: Improvement of sydnone synthesis

Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.

The Efficient Synthesis of 3-Arylsydnones Under Neutral Conditions

Various substituted aryl sydnones can be prepared in high yield under mild, neutral conditions by nitrosation of the appropriate aryl glycine with isoamyl nitrite in dimethoxyethane followed by cyclization with trifluoroacetic anhydride.